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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-03-25 20:09:37 UTC |
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| HMDB ID | HMDB0000224 |
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| Secondary Accession Numbers | - HMDB0012279
- HMDB00224
- HMDB0060151
- HMDB0060152
- HMDB12279
- HMDB60151
- HMDB60152
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| Metabolite Identification |
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| Common Name | O-Phosphoethanolamine |
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| Description | O-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine O-phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. One category termed a glycerophospholipid and the other a sphingomyelin, or more specifically within the sphingomyelin class, a sphingophospholipid. O-Phosphoethanolamine is a drug. There is, however, an experiment with mice that stated synthetic phosphoethanolamine has in vitro and in vivo anti-leukemia effects. O-Phosphoethanolamine is a very strong basic compound (based on its pKa). O-Phosphoethanolamine exists in all living species, ranging from bacteria to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine; which is mediated by the enzyme ethanolamine-phosphate cytidylyltransferase. In addition, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, O-phosphoethanolamine is involved in phosphatidylcholine biosynthesis. Outside of the human body, O-phosphoethanolamine has been detected, but not quantified in, several different foods, such as oxheart cabbages, anises, shiitakes, abalones, and teffs. This could make O-phosphoethanolamine a potential biomarker for the consumption of these foods. In October 2015, several courts in Brazil ruled in favor of plaintiffs who wanted the right to try the compound. O-Phosphoethanolamine is a potentially toxic compound. There has been ongoing controversy and litigation in Brazil with regard to its use as a cancer treatment without approval by the National Health Surveillance Agency. However, shortly after, the country's Supreme Court suspended the law. Jailson Bittencourt de Andrade, secretary for Brazil’s science and technology ministry, said the ministry plans to fund further research on the compound, but that it will be years before a determination can be made about phosphorylethanolamine's safety and efficacy in humans. As a potential drug, phosphorylethanolamine in undergoing human clinical trials. For years, Gilberto Chierice, a Chemistry Professor at the São Carlos campus of the University of São Paulo, used resources from a campus laboratory to unofficially manufacture, distribute, and promote the drug to cancer patients without it having gone through clinical testing. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Amino-ethanol dihydrogen phosphate | ChEBI | | 2-Amino-ethanol phosphate | ChEBI | | Colamine phosphate | ChEBI | | Colamine phosphoric acid | ChEBI | | Colaminphosphoric acid | ChEBI | | EAP | ChEBI | | Ethanolamine acid phosphate | ChEBI | | Ethanolamine O-phosphate | ChEBI | | Ethanolamine phosphate | ChEBI | | mono(2-Aminoethyl) phosphate | ChEBI | | Monoaminoethyl phosphate | ChEBI | | O-Phosphocolamine | ChEBI | | O-Phosphorylethanolamine | ChEBI | | OPE | ChEBI | | PE | ChEBI | | PEA | ChEBI | | PETN | ChEBI | | Phosphoethanolamine | ChEBI | | Phosphonoethanolamine | ChEBI | | Phosphoric acid 2-aminoethyl phenyl ester | ChEBI | | Phosphoryl-ethanolamine | ChEBI | | 2-Amino-ethanol dihydrogen phosphoric acid | Generator | | 2-Amino-ethanol phosphoric acid | Generator | | Colaminphosphate | Generator | | Ethanolamine acid phosphoric acid | Generator | | Ethanolamine O-phosphoric acid | Generator | | Ethanolamine phosphoric acid | Generator | | mono(2-Aminoethyl) phosphoric acid | Generator | | Monoaminoethyl phosphoric acid | Generator | | Phosphate 2-aminoethyl phenyl ester | Generator | | 2-Amino-ethanol dihydrogen phosphate (ester) | HMDB | | 2-Aminoethanol O-phosphate | HMDB | | 2-Aminoethyl dihydrogen phosphate | HMDB | | 2-Aminoethyl dihydrogen phosphate (acd/name 4.0) | HMDB | | 2-Aminoethyl phosphate | HMDB | | Colamine acid phosphate | HMDB | | Colaminephosphoric acid | HMDB | | Ethamp | HMDB | | O-Phosphonatoethanaminium | HMDB | | Phosphoryethanolamine | HMDB | | Phosphorylethanolamine | HMDB | | Phosphorylethanolamine, 3H-labeled CPD | HMDB | | Phosphorylethanolamine magnesium (1:1) salt | HMDB | | Phosphorylethanolamine zinc salt | HMDB | | Phosphorylethanolamine, cobalt (2+) (1:1) salt | HMDB | | Calcium 2-aminoethanol phosphate | HMDB | | Phosphorylethanolamine ca (1:1) salt | HMDB |
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| Chemical Formula | C2H8NO4P |
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| Average Molecular Weight | 141.063 |
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| Monoisotopic Molecular Weight | 141.019094261 |
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| IUPAC Name | (2-aminoethoxy)phosphonic acid |
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| Traditional Name | phosphorylethanolamine |
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| CAS Registry Number | 1071-23-4 |
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| SMILES | NCCOP(O)(O)=O |
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| InChI Identifier | InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6) |
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| InChI Key | SUHOOTKUPISOBE-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Organic phosphoric acids and derivatives |
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| Sub Class | Phosphate esters |
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| Direct Parent | Phosphoethanolamines |
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| Alternative Parents | |
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| Substituents | - Phosphoethanolamine
- Monoalkyl phosphate
- Alkyl phosphate
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 241 - 243 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 72 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0fki-0910000000-63541b89e6730018e48b | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fki-0910000000-63541b89e6730018e48b | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fki-0911000000-7fc066f17e2ebf6c84f8 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-9100000000-543d2d90aa663406e999 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9100000000-993b8efd11624567ec4b | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-f2fd3c258685af07afb5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-b479823e7c0ee6b5e03d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-2900000000-9cf72ee86018eb78504f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-9000000000-169b03f94a9f53bd0de4 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-9000000000-199d7ab7a4aeb040674e | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-004i-9000000000-f573b62dada3630598c3 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-38c04ce07a85a8db342c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-9100000000-b582c6b51602884756da | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-2900000000-9cf72ee86018eb78504f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-169b03f94a9f53bd0de4 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-199d7ab7a4aeb040674e | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-f573b62dada3630598c3 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-38c04ce07a85a8db342c | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-9100000000-b582c6b51602884756da | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-004i-9000000000-4335e927ba2537543f7d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-004i-9000000000-3e5f10c6e140e555b9fe | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9300000000-a9eb3cce3bf5c7453bd2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-4c92e75f13cc6c5119eb | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-5874389316d6cd66936a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002f-9800000000-b5c7c61b118c38407fa5 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9100000000-b562b8507dff78a49e4d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-dfba6ec4cc15f40c6355 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-88dc3b66f275af50de34 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 19 +/- 9.9 uM | Newborn (0-30 days old) | Both | Normal | | details | | Blood | Detected and Quantified | 4.0 +/- 2.0 uM | Adult (>18 years old) | Female | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6.0 +/- 1.1 uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6.30 (4.70-9.60) uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected and Quantified | 50.9 +/- 34.1 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 66.2 +/- 20.4 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected and Quantified | 76.2 +/- 64.8 uM | Adult (>18 years old) | Female | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | | Saliva | Detected and Quantified | 14.8 +/- 17.4 uM | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 30.53 +/- 32.79 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | <9.95 umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 0-53 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 142.263 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | <5.43 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 1.69-38.57 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 3.73-38.69 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 4.276 (1.644-6.908) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 2.15-18.55 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 8.2 +/- 2.0 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | | Urine | Detected and Quantified | <25 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 1.36-13.35 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 7.91 +/- 18.09 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 10.18 +/- 12.44 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.3 (6.50-16.4) uM | Adult (>18 years old) | Both | Brain injury | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Attachment loss | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | | Urine | Detected and Quantified | 71.48 +/- 35.869 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected and Quantified | 84 umol/mmol creatinine | Children (1-13 years old) | Female | Odontohypophosphatasia | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Traumatic brain injury |
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- Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
| | Crohn's disease |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| | Ulcerative colitis |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| | Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| | Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| | Odontohypophosphatasia |
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- Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | DB01738 |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB021911 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 990 |
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| KEGG Compound ID | C00346 |
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| BioCyc ID | PHOSPHORYL-ETHANOLAMINE |
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| BiGG ID | 1485304 |
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| Wikipedia Link | Phosphorylethanolamine |
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| METLIN ID | 5233 |
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| PubChem Compound | 1015 |
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| PDB ID | Not Available |
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| ChEBI ID | 17553 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| References |
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| Synthesis Reference | Muller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
- Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
- Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. [PubMed:7791524 ]
- Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. [PubMed:8588821 ]
- Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. [PubMed:11566853 ]
- Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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